Synthesis and NMR-Study of 1-Trimethylsilyl Substituted Silole Anion [Ph(4)C(4)Si(SiMe(3))](−)•[Li](+) and 3-Silolenide 2,5-carbodianions {[Ph(4)C(4)Si(n-Bu)(2)](−2)•2[Li](+), [Ph(4)C(4)Si(t-Bu)(2)](−2)•2[Li](+)} via Silole Dianion [Ph(4)C(4)Si](−2)•2[Li](+)

1-Trimethylsilyl, 1-R (R = Me, Et, i-Bu)-2,3,4,5-tetraphenyl-1-silacyclopentadiene [Ph(4)C(4)Si(SiMe(3))R] are synthesized from the reaction of 1-trimethylsilyl,1-lithio-2,3,4,5-tetraphenyl-1-silacyclopentadienide anion [Ph(4)C(4)SiMe(3)](−)•[Li](+) (3) with methyl iodide, ethyl iodide, and i-butyl bromide. The versatile intermediate 3 is prepared by hemisilylation of the silole dianion [Ph(4)C(4)Si](−)(2)•2[Li](+) (2) with trimethylsilyl chloride and characterized by (1)H-, (13)C-, and (29)Si-NMR spectroscopy. 1,1-bis(R)-2,3,4,5-tetraphenyl-1-silacyclopentadiene [Ph(4)C(4)SiR(2)] {R = n-Bu (7); t-Bu (8)} are synthesized from the reaction of 2 with n-butyl bromide and t-butyl bromide. Reduction of 7 and 8 with lithium under sonication gives the respective 3-silolenide 2,5-carbodianions {[Ph(4)C(4)Si(n-Bu)(2)](−)(2)•2[Li](+) (10) and [Ph(4)C(4)Si(t-Bu)(2)](−)(2)•2[Li](+) (11)}, which are characterized by (1)H-, (13)C-, and (29)Si-NMR spectroscopy. Polarization of phenyl groups in 3 is compared with those of silole anion/dianion, germole anion/dianion, and 3-silolenide 2,5-carbodianions 10 and 11.